Patent EA-000711-B1 (EA)
Title: Triazine derivatives, method producing thereof and use as herbicides
Inventor: SAITO MASATOSHI
IPC: C07D251/18
Filed: 1996-06-28
Abstract: 1. A triazine derivative of the general formula (I)    wherein X is a halogen atom, a hydroxyl group, a cyano group, a C1-C6 alkyl group, a C1-C4 alkoxy group, a C1-C4 alkylthio group, a C1-C4 alkylsulfonyl group, a C1-C6 haloalkyl group, a C1-C4 haloalkoxy group, a phenyl-substituted C1-C4 alkyl group, a phenyl group or a phenoxy group, provided that when the number of X is plural, plural substituents X may be the same as, or different from, each other or two vicinal substituents X may form a saturated or unsaturated five-membered or six-membered ring together with a carbon-carbon bond in a benzene ring, n is an integer of 0 or 1 to 4,  R is  (1) a C1-C6 alkyl group or  (2) a substituted C1-C6 alkyl group having 1 to 13 substituents of one or two kinds selected from the class consisting of  i) a halogen atom ii) a hydroxyl group and  iii) a C1-C8 alkoxy group whose alkyl portion may contain a hetero atom, and  Y is a C2-C4 alkylene group which may be substituted with 1 to 8 C1-C6 alkyl groups or a divalent group of the formula (a),   in which each of Y<1> to Y<4> is independently a hydrogen atom or a C1-C4 alkyl group. 2. The triazine derivative of claim 1, wherein X is a C1-C4 alkyl group or a halogen atom. 3. The triazine derivative of claim 1, wherein X is selected from the class consisting of methoxy, methylthio, methylsulfonyl, trifluoromethyl, trifluoromethoxy, phenoxyethyl, phenyl and phenoxy. 4. The triazine derivative of claim 2, wherein n is an integer of 1 or 2. 5. The triazine derivative of claim 4, wherein, when n is 2, each of two substituents X are independently a C1-C6 alkyl group or a halogen atom. 6. The triazine derivative of claim 1, wherein n is 0. 7. The triazine derivative of claim 1, wherein Y is a propylene group on which one C1-C4 alkyl group is subsituted. 8. The triazine derivative of claim 7, wherein Y is a propylene group on which methyl is substituted. 9. The triazine derivative of claim 1, wherein Y is a divalent group of the formula (a)   in which each of Y<1> to Y<4> is independently a hydrogen atom or a C1-C4 alkyl group. 10. The triazine derivative of claim 9, wherein each of Y<1> to Y<4> is independently a hydrogen atom or methyl. 11. The triazine derivative of claim 1, wherein R is a C1-C6 alkyl group. 12. The triazine derivative of claim 1, wherein R is a C1-C6 alkyl group on which a fluorine atom, a chlorine atom or a bromine atom is substituted. 13. The triazine derivative of claim 12, wherein R is selected from the class consisting of -CF3, -CCl3, -CH2F, -CH2Cl, -CH2Br, -C2F5, -CH2CH2F, -CHF(CH3), -CHCl(CH3), -CHBr(CH3), -CHF(CF3), -CF(CH3)2,  -CCl(CH3)2, -CBr(CH3)2, -CHF(CH2CH3), -CHCl(CH2CH3) and -CHBr(CH2CH3) groups. 14. The triazine derivative of claim 1, wherein R is a C1-C6 alkyl group on which a hydroxyl group is substituted. 15. The triazine derivative of claim 14, wherein R is selected from the class consisting of -CH2OH, -C2H4OH, -CH(OH)CH3, -CH(OH)C2H5, -C(CH3)2OH and -C(CH3)2CH2OH groups. 16. The triazine derivative of claim 1, wherein R is a C1-C6 alkyl group substituted with a group in which a heterocyclic group containing an oxygen atom and an oxygen atom bond to each other. 17. A process for the production of a triazine derivative of the general formula (I)   wherein X is a halogen atom, a hydroxyl group, a cyano group, a C1-C6 alkyl group, a C1-C4 alkoxy group, a C1-C4 alkylthio group, a C1-C4 alkylsulfonyl group, a C1-C6 haloalkyl group, a C1-C4 haloalkoxy group, a phenyl-substituted C1-C4 alkyl group, a phenyl group or a phenoxy group, provided that when the number of X is plural, plural substituents X may be the same as, or different from, each other or two vicinal substituents X may form a saturated or unsaturated five-membered or six-membered ring together with a carbon-carbon bond in a benzene ring, n is an integer of 0 or 1 to 4, R is  (1) a C1-C6 alkyl group or  2) a substituted C1-C6 alkyl group having 1 to 13 substituents of one or two kinds selected from the class consisting of  i) a halogen atom ii) a hydroxyl group and iii) a C1-C6 alkoxy group whose alkyl portion may contain a hetero atom, and Y is a C2-C4 alkylene group which may be substituted with 1 to 8 C1-C6 alkyl groups or a divalent group of the formula (a)   in which each of Y<1> to Y<4> is independently a hydrogen atom or a C1-C4 alkyl group, which comprises reacting a compound of the general formula (II)   wherein X, n and Y are as defined above and X<1> is a halogen atom, with cyanoguanidine of the formula (III)   and then reacting the reaction product with an ester of the general formula (IV) RCOOR<1> (IV), wherein R is as defined above and R<1> is a C1-C4 alkyl group. 18. A herbicide containing the triazine derivative of the general formula (I) recited in claim 1 or a salt thereof as an active ingredient.